EP0140120B1 - Ignifugeant, préparation et son utilisation dans la protection des polycarbonates - Google Patents

Ignifugeant, préparation et son utilisation dans la protection des polycarbonates Download PDF

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Publication number
EP0140120B1
EP0140120B1 EP84111049A EP84111049A EP0140120B1 EP 0140120 B1 EP0140120 B1 EP 0140120B1 EP 84111049 A EP84111049 A EP 84111049A EP 84111049 A EP84111049 A EP 84111049A EP 0140120 B1 EP0140120 B1 EP 0140120B1
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EP
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Prior art keywords
thermoplastic
weight
formula
branched
polycarbonate
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Expired
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EP84111049A
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German (de)
English (en)
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EP0140120A1 (fr
Inventor
Hans-Jürgen Dr. Kress
Klaus Dr. Kircher
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • C08K5/3417—Five-membered rings condensed with carbocyclic rings

Definitions

  • the amines of the formula (11) are known from the literature or can be obtained by processes known from the literature, as are described, for example, for 3,5-bis-tetrafluoroethylaninine in US Pat. No. 2,876,251.
  • the amount of solvent to be used is based on 1 mol of the aniline according to the invention, based on about 2.5 l of glacial acetic acid; the corresponding amount of water tractor is approx. 300 ml.
  • the new phthalimide compounds in combination with the known flame retardants for polycarbonates, the alkali salts of organic or inorganic acids, are suitable synergists for improving the flame resistance of thermoplastic, branched, aromatic polycarbonates which are only produced from halogen-free phenolic components.
  • Alkali salts of organic or inorganic acids suitable as flame retardants are mentioned, for example, in German Offenlegungsschriften No. 2703710 No. 2918882 and No. 2918883.
  • the present invention also relates to the use of the flame retardant combination according to the invention for flame-retarding thermoplastic, branched, aromatic polycarbonates from halogen-free phenolic components in amounts of 0.1 to 1% by weight, based on thermoplastic, branched, aromatic polycarbonate, of phthalimide of the formula (la) and 0.02 to 2 wt .-%, based on thermoplastic, branched, aromatic polycarbonate Alkali salt of an organic or inorganic acid.
  • the present invention also relates to a process for the flame-retardant treatment of thermoplastic, branched, aromatic polycarbonates from halogen-free phenolic components, which is characterized in that the incorporation of the flame retardant combination according to the invention as individual components or as a mixture by mixing and subsequent granulation using a twin-screw extruder at a melt temperature of 280-310 ° C takes place.
  • the optimal processing conditions are such that a throughput of 5 kg / h is achieved at a speed of 80-100 revolutions / min.
  • the unit used was an extruder from Werner and Pfleiderer with the designation ZSK 32.
  • the present invention also relates to thermoplastic molding compositions based on aromatic, branched, thermoplastic polycarbonates from halogen-free phenolic components with a content of 0.1 to 1% by weight of phthalimide of the formula (Ia) and from 0.02 to 2% by weight.
  • % of alkali salt of an inorganic or organic acid the two ranges of the weight percent each refer to thermoplastic, branched, aromatic polycarbonate without other additives.
  • Aromatic, branched, thermoplastic polycarbonates from halogen-free phenolic components are understood to mean that the diphenols, monophenols and trisphenols, tetraphenols or other branching agents to be used for the production of the polycarbonates have no halogen substituents.
  • these polycarbonates if they are produced, for example, by the phase interface process using phosgene, can still contain small amounts of residual ppm of unsaponified chlorine. In the subsequent characterization of the polycarbonates as “halogen-free”, residues of such saponifiable halogen should be disregarded.
  • phthalimides of the formula (I) according to the invention are characterized by low volatility under normal polycarbonate processing conditions.
  • the polycarbonate molding compositions according to the invention achieve combustion tests for the classification of materials (hereinafter referred to as UL 94) in the case of test specimens with 127 x 12.7 x 3.2 mm (1/8 ") or 127 x 12.7 x 1.6 mm (1/16 ") - dimensions a classification in fire class VO, d. H. they are not dripping and have an average afterburn time of ⁇ 5 s.
  • Test specimens with 127 x 12.7 x 0.8 mm (1/32 ") dimensions achieve a classification in fire class V 1, which means that they are non-dripping and have an average afterburn time of ⁇ 25 s.
  • phthalimide compounds in combination with alkali salt additives, only halogenated phthalimides being used (DOS 2 707 928, 2 740 850, 2703710).
  • organic halogen compounds such as halogenated phthalimides in combination with alkali salts and substances which reduce the tendency to drip off polycarbonates for the flame-retardant treatment of polymer alloys based on polycarbonates.
  • phthalimides of the general formula (Ia) claimed according to the invention is particularly advantageous because compounds of these classes of substances are very thermostable, non-volatile, stable to saponification and can be readily mixed into polycarbonate.
  • Suitable alkali salts of inorganic acids in the sense of the invention are, for example, those of inorganic protonic acids.
  • Inorganic protonic acids in the sense of the invention are Brönsted acids which can form alkali salts (for the expression “Brönsted acid” see Fieser & Fieser “Organic Chemistry » 1965, p. 595, Interscience Publishers NY, USA), such as, for example, meta-, ortho- or pyro-phosphoric acid and protonic acids of complex fluorometal compounds.
  • suitable alkali metal salts of organic acids are those of organic Bronsted acids with at least one carbon atom, which can form alkali metal salts.
  • Such optionally substituted organic acids can be OH- or NH-acidic compounds, such as sulfonic acids, phosphonic acids, thiophosphonic acids, NH-acidic sulfonamides or sulfonimides. They must have at least one carbon atom and can preferably contain between 2 and 30 carbon atoms.
  • the alkali salts suitable according to the invention should preferably have a pH between 5 and 9, in particular between 6.5 and 7.5, measured on 1% strength by weight solutions or suspensions of the salts in water at 20 ° C.
  • Preferred alkali salts are the potassium, sodium and lithium salts, especially the potassium salts.
  • Preferred alkali salts of organic acids are the sodium, potassium and lithium salts, but especially the potassium salts of organic sulfonic acids and phosphonic acids, the organic radicals of which may optionally be substituted by halogens such as fluorine, chlorine or bromine.
  • Examples include: sodium or potassium perfluorobutane sulfate, sodium or potassium perfluoromethane sulfonate, sodium or potassium 2,5-dichlorobenzenesulfonate, sodium or potassium 2,4,5-trichlorobenzenesulfonate, sodium or potassium (4- chlorophenyl) phosphonate, sodium or potassium methylphosphonate, sodium or potassium (2-phenylethylene) phosphonate and lithium phenylphosphonate.
  • Preferred alkali salts of inorganic acids are the sodium, potassium and lithium salts, but in particular the potassium salts of protonic acid complexes fluorometal compounds and of meta-, ortho or pyro-phosphoric acid.
  • Examples include: trisodium or tripotassium hexafluoroaluminate, disodium or dipotassium hexafluorotitanate, disodium or dipotassium hexafluorosilicate, disodium or dipotassium hexafluorozirconate, sodium or potassium pyrophosphate, sodium or potassium or potassium metaphosphate, sodium -tetrafluoroborate, sodium or potassium hexafluorophosphate and sodium or lithium phosphate.
  • Particularly suitable salts are: potassium or sodium perfluorobutanesulfonate, potassium or sodium 2,5-dichlorobenzenesulfonate, potassium or sodium 2,4,5-trichlorobenzenesulfonate, potassium hexafluoroaluminate, potassium pyrophosphate, potassium methylphosphonate, sodium hexafluoroaluminate and lithium phenylphosphonate.
  • Mixtures of the salts with one another are also suitable.
  • Halogen-free aromatic, branched, thermoplastic polycarbonates for the purposes of the present invention are obtained by reacting halogen-free diphenols, in particular dihydroxydiarylalkanes; polycondensates obtainable with phosgene or diesters of carbonic acid, where, in addition to the unsubstituted dihydroxydiarylalkanes, those are also suitable whose aryl radicals carry alkyl groups in the o- and / or m-position relative to the hydroxyl group, and which are incorporated by incorporating amounts between 0.05 and 2.0 Mol% (based on diphenols used) of three or more than three-functional compounds, for example those with three or more than three phenolic hydroxyl groups, are branched.
  • the halogen-free aromatic, branched, thermoplastic polycarbonates have average weight average molecular weights Mw between 15,000 and 100,000, preferably between 20,000 and 80,000, determined by measuring the rel. Viscosity in CH 2 Cl 2 at 25 ° C and a concentration of 0.5 g / 100 ml after appropriate calibration.
  • Suitable halogen-free diphenols are e.g. B. hydroquinone, resorcinol, 4,4'-dihydroxydiphenyl, bis (hydroxy-phenyl) alkanes such as C i -C 8 alkylene or C 2 -C 8 alkylidene bisphenols, bis (hydroxyphenyl) cycloalkanes such as for example C 5 -C 15 cycloalkylene or C 5 -C 15 cycloalkylidenebisphenols, bis (hydroxyphenyl) sulfides, ethers, ketones, sulfoxides or sulfones.
  • B. hydroquinone, resorcinol, 4,4'-dihydroxydiphenyl bis (hydroxy-phenyl) alkanes such as C i -C 8 alkylene or C 2 -C 8 alkylidene bisphenols
  • bis (hydroxyphenyl) cycloalkanes such as for example C 5 -
  • ⁇ , ⁇ '-bis (hydroxyphenyl) diisopropylbenzene and the corresponding nucleus alkylated compounds Polycarbonates based on bis- (4-hydroxy-phenyl) propane-2,2 (bisphenol A), bis- (4-hydroxy-3,5-dimethylphenyl) propane-2,2 (tetramethylbisphenol A), bis are preferred - (4-hydroxy-phenyl) -cyclohexane-1.1 (bisphenol Z) and based on trinuclear bisphenols such as ⁇ , ⁇ '-bis (4-hydroxyphenyl) -p-diisopropylbenzene.
  • Some of the compounds which can be used with three or more than three phenolic hydroxyl groups are, for example, phloroglucin, 4,6-dimethyl-2,4,6-tri- (4-hydroxyphenyl) -heptane-2,4,6-dimethyl-2,4, 6-tri- (4-hydroxyphenyl) -heptane, 1,3,5-tri- (4-hydroxyphenyl) -benzene, 1,1,1-tri- (4-hydroxyphenyl) -ethane, tri- (4-hydroxyphenyl ) -phenylmethane, 2,2-bis- [4,4-bis- (4-hydroxyphenyl) cyclohexyl] propane, 2,4-bis- (4-hydroxyphenyl-isopropyl) phenol, 2,6-bis- (2'-hydroxy-5'-methylbenryl) -4-methylphenol, 2- (4-hydroxyphenyl) -2- (2,4-dihydroxyphenyl) propane, hexy- (4- (4-hydroxyphenyl
  • Suitable chain terminators for regulating the molecular weight are, for example, phenol and alkylphenols, which are used in the known amounts.
  • the aromatic, branched, thermoplastic polycarbonates are prepared in a known manner, for example by the interfacial process or by the process in homogeneous solution.
  • the aromatic, thermoplastic polycarbonates can also be produced by the known transesterification process.
  • Particularly preferred polycarbonates for the purposes of the present invention are branched polycarbonates based on bisphenol-A with a branching content of 0.3 to 1.0 mol%, based on moles of bisphenol-A.
  • Suitable amines for the preparation of the penthalimides of the formula (Ia) are e.g. B.
  • Suitable phthalimide compounds of the formula (Ia) are e.g. B.
  • the flame retardant combinations according to the invention can be prepared beforehand by mixing the individual components or as a concentrate in polycarbonate and can be stored, for example, until use.
  • the new flame retardant combination can be incorporated individually in the form of its components or together in the polycarbonates, for example by mixing and then granulating the material using a twin-screw extruder at 280 to 310 ° C.
  • the molding compositions based on polycarbonate and a flame retardant combination can also contain other additives customary in polycarbonate chemistry, such as, for example, pigments, dyes, fillers, stabilizers or mold release agents.
  • the molding compositions according to the invention can be processed into moldings or films.
  • Moldings are manufactured using the injection molding process at a temperature of 300-310 ° C.
  • the molding compositions according to the invention can be used, for. B. in the electrical sector for switch panels, sockets, power strips, switch boxes, etc., in the household sector for housing parts of irons, coffee machines and large appliances such. B. for computer case parts.
  • polycarbonate samples are made into rods measuring 127 x 12.7 x 0.8 (or 1.6 or 3.2) mm (5.00 x 0.05 x 1 / 32) (or 1/16 or 1/8 inches) shaped.
  • the rods are mounted vertically so that the underside of the test specimen is 305 mm above a strip of bandaging material.
  • Each test stick is ignited individually by means of two successive ignition processes of 10 s duration, the burning properties after each ignition process are observed and the sample is then evaluated.
  • a Bunsen burner with a 10 mm (3/8 inch) raised blue flame of natural gas with a heat content of 3.73 x 10 4 kJ / m 3 (1,000 BTU per cubic foot) is used to ignite the sample.
  • the UL 94 V 0 classification includes the properties of materials described below that have been tested in accordance with UL 94 regulations.
  • the polycarbonates in this class do not contain any Samples burning longer than 10 s after each exposure to the test flame do not show a total flame time of more than 50 s when exposed to each sample set twice; they do not contain samples that burn completely down to the retaining clip attached to the top of the sample; they have no samples which ignite the cotton wool arranged below the sample by burning drops or particles; they also do not contain any samples that glow more than 30 s after the test flame has been removed.
  • UL 94 classifications refer to samples that are less flame retardant and self-extinguishing and that emit flaming drops or particles. These classifications are referred to as UL 94 V-1 and V-2.
  • the polycarbonates within the scope of this invention characteristically exhibit the properties required for UL 94 V 0 classification.
  • the glacial acetic acid is distilled off and the end product is boiled in toluene, filtered hot and cooled.
  • the precipitated crystals are slurried with petroleum ether, suction filtered and dried.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Indole Compounds (AREA)
  • Fireproofing Substances (AREA)

Claims (7)

1. Phtalimides de formule (I)
Figure imgb0013
dans laquelle
n est un nombre entier de 1 à 12 et
R représente H ou F, sous réserve que lorsque n = 1, R ne représente pas F.
2. Procédé de production de phtalimides de formule I, caractérisé en ce qu'on fait réagir l'anhydride d'acide phtalique avec une amine de formule (II)
Figure imgb0014
dans laquelle
n est un nombre entier de 1 à 12 et
R représente H ou F, sous réserve que lorsque n = 1, R ne représente pas F,

en quantités équimolaires à environ 117 °C et en utilisant simultanément de l'acide acétique cristallisable comme solvant et du cyclohexane comme substance entraînant l'eau.
3. Mélanges retardateurs de flamme, constitués
a) de 0,1 à 1 partie en poids d'un phtalimide de formule (la)
Figure imgb0015
dans laquelle
n est un nombre entier de 1 à 12, et
R représente H ou F,

et
b) de 0,02 à 2 parties en poids d'un sel alcalin d'un acide organique ou inorganique.
4. Utilisation du mélange retardateur de flamme suivant la revendication 3, pour l'ignifugeage de polycarbonates aromatiques thermoplastiques ramifiés dérivés de composants phénoliques non halogénés, dans des quantités de 0,1 à 1% en poids, par rapport au polycarbonate, de phtalimide de formule (la) suivant la revendication 3, et de 0,02 à 2 % en poids, par rapport au polycarbonate, d'un sel alcalin d'un acide organique ou inorganique.
5. Procédé d'ignifugeage de polycarbonates aromatiques thermoplastiques ramifiés, dérivés de composants phénoliques non halogénés, caractérisé en ce que l'incorporation du mélange retardateur de flamme suivant la revendication 3 comme composant individuel ou coma mélange est effectuée par mélange, puis granulation sur une extrudeuse à deux arbres à une température du mélange de 280 à 310°C, de préférence de 290 à 300 °C, et un débit de 5 kg/h est atteint pour une vitesse de rotation de 80 à 100 tours par minute.
6. Mélanges thermoplastiques à mouler à base de polycarbonates aromatiques thermoplastiques ramifiés, dérivés de composants phénoliques non halogénés, ayant une teneur de 0,1 à 1 % en poids en phtalimide de formule (la) suivant la revendication 3 et une teneur de 0,02 à 2 % en poids d'un sel alcalin d'un acide organique ou inorganique, les deux intervalles de pourcentages en poids se rapportant chacun au polycarbonate aromatique thermoplastique ramifié sans autres additifs.
7. Mélanges à mouler thermoplastiques suivant la revendication 6, caractérisés en ce que le polycarbonate thermoplastique est un polycarbonate ramifié à base de Bisphénol A ayant une teneur en groupes ramifiants de 0,3 à 1,0 mole % par rapport au Bisphénol A.
EP84111049A 1983-09-26 1984-09-17 Ignifugeant, préparation et son utilisation dans la protection des polycarbonates Expired EP0140120B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3334822 1983-09-26
DE19833334822 DE3334822A1 (de) 1983-09-26 1983-09-26 Neue flammschutzmittel, ihre herstellung und ihre verwendung zur flammfestausruestung von polycarbonaten

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EP0140120A1 EP0140120A1 (fr) 1985-05-08
EP0140120B1 true EP0140120B1 (fr) 1987-11-11

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EP (1) EP0140120B1 (fr)
JP (2) JPS6087263A (fr)
DE (2) DE3334822A1 (fr)

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US5618907A (en) 1985-04-23 1997-04-08 The Boeing Company Thallium catalyzed multidimensional ester oligomers
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Also Published As

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JPH0322876B2 (fr) 1991-03-27
DE3334822A1 (de) 1985-04-04
US4615832A (en) 1986-10-07
US4657955A (en) 1987-04-14
JPH03123772A (ja) 1991-05-27
JPS6087263A (ja) 1985-05-16
EP0140120A1 (fr) 1985-05-08
DE3467347D1 (en) 1987-12-17

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